Cationic sugar surfactants from ethoxylated ammonium compounds and reducing saccharides

ABSTRACT

The present invention relates to cationic sugar surfactants with improved biodegradability that can be used as hydrotropes for surfactants, especially for nonionic alkylene oxide adducts in alkaline solutions, and as cleaners for hard surfaces. The cationic sugar surfactants contain at least one hydrocarbon group with 6-24 carbon atoms and at least one quaternary ammonium group where at least one substituent is an alkyleneoxy containing group which is connected to a saccharide residue by a glycosidic bond. They are obtained from ethoxylated quaternary ammounium compounds and reducing saccharides or alkyl glycosides.

[0001] The present application is a continuation of International PatentApplication No. PCT/SE98/01433, filed on Aug. 3, 1998, which claimspriority of Sweden Patent Application No. 9703089-4, filed on Aug. 27,1997.

FIELD OF THE INVENTION

[0002] The present invention relates to cationic sugar surfactants withimproved biodegradability that can be used as hydrotropes forsurfactants, especially for nonionic alkylene oxide adducts in alkalinesolutions, and as cleaners for hard surfaces. They are obtained fromethoxylated quaternary ammounium compounds and reducing saccharides oralkyl glycosides.

BACKGROUND OF THE INVENTION

[0003] Surface active nonionic alkylene oxide adducts are widely used asessential degreasing and/or dispersing components in alkaline cleaningcompositions. Their solubility in cleaning composition concentrates is,however, limited in the presence of high amounts of electrolytes, suchas alkali and/or alkaline complexing agents.

[0004] It is prior known that cationic surfactants, such as ethoxylatedfatty amines (about 14-20 moles ethylene oxide per mol fatty amine) thathave been quaternized by an alkylating agent, e.g. methyl chloride ordimethyl sulfate, are excellent hydrotropes for nonionic alkylene oxideadducts and are also good cleaners themselves. However, from anenvironmental point of view they are less desirable, since they are notreadily biodegradable.

[0005] The main purpose of the present invention is to provide productsthat are excellent hydrotropes for surfactants.

[0006] Another purpose is to provide hydrotropes with improvedbiodegradability over the prior used cationic surfactants.

[0007] Still another purpose is to provide hydrotropes which contributeto the cleaning performance of the surfactants.

[0008] It has now been found that said main purpose is achieved byusing, as a hydrotrope a cationic sugar surfactant containing at leastone hydrocarbon group with 6-24 carbon atoms and at least one quaternaryammonium group where at least one substituent is an alkyleneoxycontaining group which is connected to a saccharide residue by aglycosidic bond.

SUMMARY OF THE INVENTION

[0009] The present invention generally relates to a cationic sugarsurfactant containing at least one hydrocarbon group with 6-24 carbonatoms and at least one quaternary ammonium group where at least onesubstituent is an alkyleneoxy containing group which is connected to asaccharide residue by a glycosidic bond, and more particularly, the useof said sugar surfactant as a hydrotrope for surfactants.

DETAILED DESCRIPTION OF THE INVENTION

[0010] In accordance with the present invention, new hydrotropes whichcontribute to the cleaning performance of the surfactants have beenfound. These hydrotropes comprise a cationic sugar surfactant containingat least one hydrocarbon group with 6-24 carbon atoms and at least onequaternary ammonium group where at least one substituent is analkyleneoxy containing group which is connected to a saccharide residueby a glycosidic bond.

[0011] Preferably the substituent has the formula (AO)_(s)(G)_(g) whereAO is an alkyleneoxy group with 2-4 carbon atoms, G is a saccharideresidue, g is a number from 1 to 10 and s is a number from 1 to 12.

[0012] The cationic sugar surfactant according to the invention may beproduced by reacting

[0013] a) an amine compound containing at least one hydrocarbon groupwith 6-24 carbon atoms and at least one quaternary ammonium group, whereat least one substituent is a hydroxyalkyl containing group, and

[0014] b) a reducing saccharide or an alkyl glycoside where the alkylgroup has 1-8 carbon atoms,

[0015] at least partially in the presence of an acid. The substituentattached to the quaternary ammonium group has preferably the formula(AO)_(s)(G)_(g), where AO is an alkyleneoxy group with 2-4 carbon atoms,G is a saccharide residue, g is a number from 1 to 10 and s is a numberfrom 1 to 12.

[0016] Suitable sugar surfactants according to the invention have theformula

[0017] where R is an aliphatic group with 6-24, preferably 8-20 carbonatoms; R₁ is an aliphatic group with 1-4 carbon atoms or(AO)_(s)(G)_(p); R₂, R₃ and R₄ are a group (AO)_(s)(G)_(p), an aliphaticgroup with 1-24 carbon atoms or a hydroxyalkyl group with 2-4 carbonatoms; AO is an alkyleneoxy group with 2-4 carbon atoms; s is 0-12,preferably 1-6 and Σs=1-25, preferably 3-15; G is a saccharide residuewhich is connected to the rest of the molecule by a glycosidic bond andp (the degree of polymerisation) is 0-10 and Σp=1-20; r=0-3; y=2-3; X=COor COO(AO)_(t)(C_(q)H_(2q)) or O(AO)_(t)(C_(q)H_(2q)); n=0 or 1; n₁ is 0except when X is CO, then n₁ is 1; q=2-4; t=0-2; u=0 or 1 and v=0 or 1,provided that the sum (v+Σu) is 1-3, preferably 1; Z is an anion,preferably a monovalent anion, such as Cl⁻ or methyl sulphate and z isthe charge of the anion Z. The nitrogen atoms where u or v is 1 arequaternary and thus have a permanent positive charge. These cationicsugar surfactants have, in comparison with the prior known cationichydrotropes, an essentially improved biodegradability. They are alsocomparable or better hydrotropes for surfactants, especially nonionicalkoxylates, and combine the improved biodegradability and goodhydrotropy with a surprisingly large contribution to the cleaningperformance of cleaning compositions as well as a valuable dispersingeffect.

[0018] The product (I) can be produced by reacting a) a reducingsaccharide or an alkyl glycoside and b) a quaternary ammonium compoundhaving the formula

[0019] where R₆ is independently an aliphatic group with 1-4 carbonatoms or —CH₂CH₂OH; R₇, R₈ and R₉ independently are a group (AO)_(s), analiphatic group with 1-24 carbon atoms or a hydroxyalkyl group with 2-4carbon atoms; l=0 or 1 and k=0 or 1, provided that the sum (k+Σl) is1-3, preferably 1; and R, AO, s, X, n, n₁, y and r have the same meaningas in formula I. The nitrogen atoms where k or l is 1 are quaternary andthus have a permanent positive charge. Since compounds II are ratherhydrophobic due to a limited number of oxyethylene units, they exhibitno or only limited hydrotropic effects. Also the cleaning ability ofcompounds having the formula II is poor. The obtained reaction mixturecontains essential amounts of both the cationic sugar surfactant I andthe quaternary ammonium compound II. This product mixture canadvantageously be used without any purification as a hydrotrope.Normally the ratio between the cationic sugar surfactant I and thequaternary ammonium compound II is from 1:3 to 9:1.

[0020] Suitable examples of the cationic sugar surfactants and thequaternary ammonium compounds are those having the formulae

[0021] where R is an aliphatic group with 6-24, preferably 8-20 carbonatoms; R₁ is an aliphatic group with 1-4 carbon atoms or the groupC₂H₄O(G)_(p); G is a saccharide residue that is connected to thepolyethyleneoxy chain by a glycosidic bond and p (the degree ofpolymerisation) is 0-10, preferably 0-5, Σp being 1-15, preferably 1-8;EO is an ethyleneoxy group; s is 0-12; Σs is 2-15, preferably 5-12; Zand z have the meaning mentioned in formula I and

[0022] where R, R₁, EO, z, Z and s have the same meaning as in formulaIII except that p in the group R₁ is 0, respectively.

[0023] Suitable examples of hydrophobic groups R in formula 1-IV are:hexyl, 2-ethylhexyl, octyl, decyl, cocoalkyl, lauryl, oleyl, rape seedalkyl and tallow alkyl.

[0024] The cationic sugar surfactants III are easily produced byreacting a reducing saccharide and the quaternary ammonium compound offormula IV. The reaction mixtures containing essential amounts of bothcompound III and IV are preferably used as hydrotropes without anyseparation of the compounds, mainly because such a separation is acostly operation. The relation between cationic sugar surfactant and thequaternary ammonium compound could vary between 1:3 and 9:1, preferablybetween 2:3 and 9:1.

[0025] Cationic surfactants containing sugar residues are known by thepublications DE 4 413 686 and JP 4-193891. In DE 4 413 686 surfactantscontaining quaternary ammonium groups are prepared by reactingglycosides with quaternary halogenated compounds or quaternary epoxycompounds. The linkage between the sugar residue and the cationic partis an ether linkage. The products could also be prepared by firstreacting the glycoside with a halogenated compound followed by reactingwith an amine. The applications for these products are for example ascomponents in detergent mixtures.

[0026] In JP 4-193891 cationic sugar surfactants are prepared by thefollowing procedure: A reducing saccharide or an alkyl glycoside isreacted with a polyalkyleneglycol halohydrin in the presence of an acidcatalyst to obtain a polyoxyalkylene halohydrin glycoside. This productis further reacted with an amine compound, whereby the chlorine isdisplaced, and the resulting amine is then quaternized by e.g. methylchloride or dimethyl sulphate. The quaternization could also take placeby directly reacting the halogenated intermediate with a tertiary amine.

[0027] These products are used as mild surfactants with goodbiodegradability. However, the procedure of making them requires theproduction of the intermediate polyalkyleneglycol monohalohydrin wherethe starting material is 2-chloroethanol, which nowadays is onlyproduced on a small scale and further is a highly toxic and irritantsubstance. To obtain the polyalkyleneglycol monochlorohydrine, the2-chloroethanol is alkoxylated in the presence of an acid catalyst. Theglycosidation process which then follows, makes use of a laborious andcostly work-up procedure with distillation or solvent extraction, whichis performed in order to get rid of the unreacted polyalkyleneglycolhalohydrin.

[0028] The process involves at least the following steps; preparation ofthe polyalkyleneglycol halohydrin, preparation of polyoxyalkylenehalohydrin glycoside and at last preparation of the quaternary ammoniumalkylaminopolyoxyalkylene glycoside by reaction with a tertiary amine.If a primary or secondary amine is used instead, additional steps arerequired to obtain a quaternarization. Furthermore, in the lastmentioned case inorganic salt is produced, which is removed by filteringthe product.

[0029] The present invention utilizes a different synthetic route toobtain cationic sugar surfactants. The general procedure for makingproducts with the formula I according to this invention involves theone-step reaction between a quaternary alkoxylated ammonium compound IIand a reducing saccharide or an alkyl glycoside. The compound II isobtained by standard procedures known to those skilled in the art. Thereaction between II and the saccharide is a glycosidation and can beperformed as follows: Compound II is heated to a reaction temperature offrom 85 to 120° C. and the saccharide is added in an amount of between0.5 and 12, preferably between 1.5 and 6 mole saccharide/mole quaternaryammonium compound. Depending on the amine used, the cationic sugarsurfactant I can contain one, two, three or more saccharide residues(G)_(p), where G and p have the meaning mentioned in formula I. Thesaccharide reactant is preferably added in excess with regard to thenumber of glycoside bonds desired, since the saccharide also has atendency to condensate with more saccharide units. This condensation isindicated in the formulae by the polymerisation degree p. The reactionis catalyzed by strong acid, e.g. p-toluenesulphonic acid or sulphuricacid, which may be added to the reaction mixture in an amount of between0.1 and 4, preferably between 0.7 and 2.1 mole % of compound II. If thecompound II is reacted with an alkyl glycoside, the process is atrans-glycosidation reaction. To aid the removal of water or alcoholfrom the reaction mixture, the process is carried out under reducedpressure (50-70 mbar). The reaction time is very dependent on thetemperature and varies between less than one hour to six hours. When nomore water or alcohol distills off the product is neutralized.

[0030] The method for producing the cationic sugar surfactant of thisinvention is quick and convenient. The starting materials are readilyavailable and the process does not require any work-up of the reactionmixture. There is no need to add an excess of the quaternary ammoniumcompound in the glycosidation reaction. Rather the saccharide or alkylglycoside is added in excess to give products with several saccharideunits attached.

[0031] In aqueous alkaline solution the cationic sugar surfactantsaccording to the present invention exhibit excellent hydrotropic effectsfor surfactants like nonionic alkoxylates. These alkoxylates couldcontain a hydrophobic group of 8-50 carbon atoms, which preferably is ahydrocarbon group or an acyl group containing from 8 to 24 carbon atoms.Suitable examples of such nonionic surfactants are alkylene oxideadducts obtained by alkoxylation of an alcohol, an amine or an amide.One example is compounds having the formula

R′O(AO)_(a)H  (V)

[0032] wherein R′ is a hydrocarbon group having 8-18 carbon atoms, a isfrom 2-12, preferably 3-10, and AO is an alkyleneoxy group having 2-4carbon atoms, the number of ethyleneoxy groups being at least 50% of thetotal number of alkyleneoxy groups. The R′ group may be branched orstraight, saturated or unsaturated, aromatic or aliphatic. Examples ofhydrocarbon groups R′ are: 2-ethylhexyl, octyl, decyl, cocoalkyl,lauryl, oleyl, rape seed alkyl, tallow alkyl, octylphenol andnonylphenol. Especially suitable hydrocarbon groups are those obtainedfrom oxoalcohols, Guerbet alcohols, methyl substituted alcohols with 2-4groups having the formula —CH(CH₃)—included in the alkyl chain, andstraight alcohols.

[0033] Another example of suitable nonionic surfactants are compoundshaving the formula

[0034] wherein R″ is a hydrocarbon group or an acyl group having 8-18carbon atoms, AO has the same meaning as in formula V and the sum of b1and b2 is 2-12, preferably 3-10. The hydrocarbon group and the acylgroup can be aromatic or aliphatic, branched or straight, saturated orunsaturated. Examples of suitable groups are 2-ethylhexyl, octyl, decyl,cocoalkyl, lauryl, oleyl, rape seed alkyl, tallow alkyl and thecorresponding aliphatic acyl groups. If R″ in the formula VI is an acylgroup, preferably one of b1 and b2 is 0, whereas if the nitrogen atom isan amine nitrogen, b1 and b2 are both preferably different from zero.

[0035] The cationic sugar surfactants of the invention are normally usedin alkaline compositions having a pH-value above 8, preferably from9-13, for use in the cleaning of hard surfaces, like degreasing of metaland plastic, dish washing and car washing. A suitable formulatedcomposition concentrate may contain

[0036] a) 0.5-20% by weight of a surface active nonionic alkylene oxideadduct,

[0037] b) 0.2-20% by weight of a mixture consisting of a cationic sugarsurfactant according to formula I, and a compound of formula II presentin a weight ratio of from 1:3 to 9:1,

[0038] c) 0.5-30% by weight of alkali and/or polyelectrolytes likealkaline complexing agents,

[0039] d) 0-10% by weight of other conventional components in cleaningcompositions, like other surfactants, other hydrotropes, thickeningagents, solvents, colourants, soil antiredeposition agents, defrostingstabilizers, preservatives, corrosion inhibitors, foam regulators, etc,and

[0040] e) 30-98.8% by weight of water.

[0041] The concentrates are normally diluted with water prior to use,and the ready-to-use solution may be diluted to a concentration of from0.05% to 15% by weight of alkali and/or alkaline complexing agents.

[0042] The complexing agent in the concentrate can be inorganic as wellas organic. Typical examples of inorganic complexing agents used in thealkaline cleaning concentrate are alkali salts of silicates andphosphates, such as sodium tripolyphosphate, sodium orthophosphate,sodium pyrophosphate, sodium phosphate, polymer sodium phosphates andthe corresponding potassium salts. Typical examples of organiccomplexing agents are alkaline aminopolyphosphonates, organicphosphates, polycarboxylates, such as citrates; aminocarboxylates, suchas sodium nitrilotriacetate (Na₃NTA), sodiumethylenediaminetetraacetate, sodium diethylenetriaminepentaacetate,sodium 1,3-propylenediaminetetraacetate and sodiumhydroxyethylethylenediaminetriacetate.

[0043] The following examples are illustrative of the invention and arenot to be construed as limiting thereof.

[0044] In Examples 1-5 the production of some representatives of thequaternary sugar surfactants of the present invention is described. InExample 6 the improved biodegradability of the quaternary sugarsurfactants as compared to prior art hydrotropes is demonstrated. InExamples 7 and 8, it is shown that the cationic surfactants of thepresent invention are better hydrotropes than the cationic hydrotropiccompounds of the prior art both with respect to the amount of hydrotropeneeded to obtain a clear solution with given concentrations of nonionicsurfactant and alkaline complexing agents, and with respect to theamount of complexing agent possible to include in an isotropic alkalinecleaning concentrate. In Example 9 the improved cleaning ability ascompared to prior art hydrotropes is demonstrated.

EXAMPLE 1

[0045] 1 mole of a cocoamine ethoxylate (1 mole cocoamine+8 moleethylene oxide) quaternized with methyl chloride was heated to 100° C.Two moles of glucose and 1.4 mole % (referring to the quaternarycompound) of p-toluenesulphonic acid was added to the quaternaryammonium compound. The reaction mixture was kept between 98 and 106° C.under reduced pressure (50-70 mbar) for 2.5 hours. Finally the productwas neutralised by first adding sodium methylate and then sodiumcarbonate. The product mixture contained about 42% (w/w) unglucosidisedstarting material and 2.0% free glucose according to GC. The structureof a glucosidised product according to formula III, where R=cocoalkyl,R₁=methyl, Σs=8, Σp=2 and Z=Cl was confirmed by ¹H and ¹³C-NMR.

EXAMPLE 2

[0046] The same procedure as described in Example 1 was followed, butwith the exception that 3 moles of glucose was added, the temperaturewas between 95 to 99° C. and the reaction time was 3.3 hours. Theproduct mixture contained about 34% (w/w) unglucosidised material and 1%free glucose. A glucosidised product according to formula III, whereR=cocoalkyl, R₁=methyl, Σs=8, Σp=3 and Z=Cl was obtained.

EXAMPLE 3

[0047] 1 mole of an oleylamine ethoxylate (1 mole oleylamine+12 moleethylene oxide) quaternised with methyl chloride, was reacted with 3moles of glucose by the procedure described i Example 1, with theexception that the reaction temperature was between 98 to 100° C. andthe reaction time was 3.75 hours. The product mixture contained about55% (w/w) unglucosidised starting material and 1.7% free glucose. Aglucosidised product according to formula III, where R=oleyl, R₁=methyl,Σs=12, Σp=3 and Z=Cl was obtained.

EXAMPLE 4

[0048] 1 mole of an oleylamine ethoxylate (1 mole oleylamine+11 moleethylene oxide), quaternised with methyl chloride, was reacted with 3moles of glucose by the procedure described in Example 1, with theexception that the reaction temperature was 96° C. and the reaction timewas 4 hours. The product mixture contained about 63% (w/w)unglucosidised starting material and 8.7% free glucose. A glucosidisedproduct according to formula III, where R=oleyl, R₁=methyl, Σs=11, Σp=3and Z=Cl was obtained.

EXAMPLE 5

[0049] 1 mole of a cocoamine ethoxylate (1 mole cocoamine+8 moleethylene oxide), quaternised with ethylene oxide, was reacted with 4moles of glucose by the procedure described in Example 1, with theexception that the reaction temperature was between 90 to 97° C. and thereaction time was 3.5 hours. The product mixture contained about 39%(w/w) unglucosidised starting material and 4% free glucose. Aglucosidised product according to formula III, where R=cocoalkyl,R₁=C₂H₄O(G)_(p), Σs=8, Σp=4 and Z=Cl was obtained.

EXAMPLE 6

[0050] Biodegradability tests were performed with the “closed bottletest” as described in OECD Test 301D. Cocoamine with 15 oxyethyleneunits, that has been quaternised by dimethyl sulphate, which is anexample of prior art hydrotrope, was used as a reference. This compoundreached 17% biodegradation after 28 days. The product obtained inExample 1 exhibited 41% biodegradation at the same occasion with thesame test method. Accordingly, the biodegradation was more than doubledwith the product in Example 1 as compared to the prior art cationichydrotrope that was used as a reference. TABLE 1 Product Example nr %biodegradation 1 41 2 31 3 — 4 35 5 — Reference 17

EXAMPLE 7

[0051] To evaluate the efficiency as a hydrotrope of the cationic sugarsurfactants of this invention the following formulation was used:Ingredient % by weight Nonionic surfactant 5 Sodium metasilicate × 5H₂O4 Tetrapotassium pyrophosphate 6 Reaction product containing hydrotropeX Water [100 − (15 + X)]

[0052] The nonionic surfactant used was a C₉₋₁₁ alcohol with a linearityabove 80% w/w that had been ethoxylated with 4 moles of ethylene oxideper mole alcohol in the presence of a narrow range catalyst. X is theamount of reaction product containing hydrotrope from Example 1-5 neededto obtain a clear solution between 10 and 40° C. The reference used isthe same as the reference for the biodegradability tests. The resultsfrom this investigation of hydrotropic efficiency are collected in Table2. TABLE 2 % by weight % active amount Formula of hydrotrope ofglucosidised tion no Hydrotrope mixture hydrotrope used I Example 1 31.7 II Example 2 2.9 1.9 III Example 3 3.3 1.4 IV Example 4 3.0 0.8 VExample 5 4.9 2.8 A Reference 3.0 3.0

EXAMPLE 8

[0053] To solutions containing 5% nonionic surfactant and differentamounts of Na₃NTA kept at 40° C. the hydrotropes were added in thesmallest amounts possible to make the turbid solutions clear. Todetermine the clearness interval the mixtures were then heated up to thepoint when they went turbid again and thereafter chilled to 0° C. Thenonionic surfactant and the reference used are the same as in Example 7.The results from the investigation are collected in Table 3. TABLE 3 %by weight of mixture Hydrotrope, containing % by weight ClearnessExample No hydrotrope Na₃NTA interval, ° C. 4 3.5 10 0-79 4 4.5 15 0-604 6 20 0-55 4 10 25 0-48 Reference 2.5 10 0-45 Reference 4 15 0-43

EXAMPLE 9

[0054] To evaluate the cleaning efficiency of the formulations inExample 7 containing the cationic sugar surfactants the followingcleaning test was used: White painted plates were smeared with anoil-soot mixture obtained from diesel engines. 25 ml of the testsolutions, in this case the formulations in Example 7 diluted 1:40, arepoured onto the top of the oil-smeared plates and left there for oneminute. The plates are then rinsed off with a rich flow of water. Allsolutions and the water are kept at a temperature of about 15-20° C. Allreference solutions are placed on the same plate as the test solutions.The cleaning ability is measured with a Minolta Chroma Meter CR-200reflectometer using the lightness values, and the result is presented asthe remaining % loss of lightness. Accordingly, the lower the valuesare, the better the cleaning ability. The results are collected in Table4. TABLE 4 Active content % loss of Formula- of hydrotrope lightness attion nr in formulation 1:40 dilution I 1.7 4.6 II 1.9 6.1 III 1.4 5.3 IV0.8 3.6 V 2.8 5.0 A 3.0 14.4

[0055] As can bee seen from Table 4, the cationic sugar surfactants aremore efficient cleaners than the prior art hydrotropes.

We claim:
 1. A method of increasing the solubility of a surfactantcomposition which comprises adding a hydrotrope to said composition,said hydrotrope comprising a cationic sugar surfactant containing atleast one hydrocarbon group with 6-24 carbon atoms and at least onequaternary ammonium group where at least one substituent is analkyleneoxy containing group which is connected to a saccharide residueby a glycosidic bond.
 2. The method of of claim 1 wherein in saidcationic sugar surfactant, the substituent has the formula(AO)_(s)(G)_(g), where AO is an alkyleneoxy group with 2-4 carbon atoms,G is a saccharide residue, g is a number from 1 to 10 and s is a numberfrom 1-12.
 3. The method of claim 1 wherein said cationic sugarsurfactant has the formula

where R is an aliphatic group with 6-24 carbon atoms; R₁ is an aliphaticgroup with 1-4 carbon atoms or (AO)_(s)(G)_(p); R₂, R₃ and R₄independently are a group (AO)_(s)(G)_(p), an aliphatic group with 1-24carbon atoms or a hydroxyalkyl group with 2-4 carbon atoms; AO is analkyleneoxy group with 2-4 carbon atoms; s is 0-12 and Σs=1-25; G is asaccharide residue which is connected to the rest of the molecule by aglycosidic bond and p (the degree of polymerisation) is 0-10; Σp=1-20;r=0-3; y=2-3; X=CO or COO(AO)_(t)(C_(q)H_(2q)) orO(AO)_(t)(C_(q)H_(2q)); n=0 or 1; n₁ is 0 except when X is CO, then n₁is 1; q=2-4; t=0-2; u=0 or 1 and v=0 or 1, provided that the sum (v+Σu)is 1-3; Z is an anion and z is the charge of the anion Z.
 4. The methodof claim 3, where the cationic sugar surfactant is present in a mixturewith a quaternary ammonium compound having the formula

where R₆ is independently an aliphatic group with 1-4 carbon atoms or—CH₂CH₂OH; R₇, R₈, and R₉ independently are a group (AO)_(s), analiphatic group with 1-24 carbon atoms or a hydroxyalkyl group with 2-4carbon atoms; 1=0 or 1 and k=0 or 1, provided that the sum (k+Σ1) is1-3; and R is an aliphatic group with 6-24 carbon atoms or(AO)_(s)(G)_(p), AO is an alkyleneoxy group with 2-4 carbon atoms, s is0-12 and Σs=1-25, X=CO or COO(AO)_(t)(C_(q)H_(2q)) orO(AO)_(t)(C_(q)H_(2q)); n=0 or 1; n₁ is 0 except when X is CO, then n₁is 1, r=0-3; y=2-3, in a weight ratio 1:3-9:1.
 5. The method of claim 3wherein the cationic sugar surfactant has the formula

where R is an aliphatic group with 6-24 carbon atoms; R₁ is an aliphaticgroup with 1-4 carbon atoms or the group C₂H₄O(G)_(p); G is a saccharideresidue that is connected to the polyethyleneoxy chain by a glycosidicbond and p (the degree of polymerisation) is 0-10; Σp is 1-15; EO is anethyleneoxy group; s is 0-12; Σs is 2-15; Z is an anion and z is thecharge of the anion Z.
 6. The method of claim 5, wherein the cationicsugar surfactant is present in a mixture with a quaternary ammoniumcompound having the formula

where R is an aliphatic group with 6-24 carbon atoms; R₁ is an aliphaticgroup with 1-4 carbon atoms or the group C₂H₄O(G)_(p); G is a saccharideresidue that is connected to the polyethyleneoxy chain by a glycosidicbond and p (the degree of polymerisation) is 0-10; Σp is 1-15; EO is anethyleneoxy group; s is 0-12; Σs is 2-15; Z is an anion and z is thecharge of the anion Z, except that p in the group R₁ is 0, in a weightratio 1:3-9:1.
 7. The method of claim 1 wherein the cationic sugarsurfactant is used as a hydrotrope for surface active nonionic alkyleneoxide adducts.
 8. A method of producing a cationic sugar surfactantaccording to claim 1 wherein a) an amine compound containing at leastone hydrocarbon group with 6-24 carbon atoms and at least one quaternaryammonium group, where at least one substituent is an hydroxyalkylcontaining group, and b) a reducing saccharide or an alkyl glycosidewhere the alkyl group has 1-8 carbon atoms are reacted at leastpartially in the presence of an acid.
 9. The method of claim 8 whereinthe substituent has the formula (AO)_(s)H, where where AO is analkyleneoxy group with 2-4 carbon atoms and s is a number from 1-12. 10.The method of claim 8 wherein the amine compound is of formula II

where R₆ is independently an aliphatic group with 1-4 carbon atoms or—CH₂CH₂OH; R₇, R₈, and R₉ independently are a group (AO)_(s), analiphatic group with 1-24 carbon atoms or a hydroxyalkyl group with 2-4carbon atoms; 1=0 or 1 and k=0 or 1, provided that the sum (k+Σ1) is1-3; and R is an aliphatic group with 6-24 carbon atoms or(AO)_(s)(G)_(p), AO is an alkyleneoxy group with 2-4 carbon atoms, s is0-12 and Σs=1-25, X=CO or COO(AO)_(t)(C_(q)H_(2q)) orO(AO)_(t)(C_(q)H_(2q)); n=0 or 1; n₁ is 0 except when X is CO, then n₁is 1, r=0-3; and y=2-3.
 11. The method of producing a cationic sugarsurfactant according to claim 10, where the reactant a) is an aminecompound with the formula IV

where R is an aliphatic group with 6-24 carbon atoms; R₁ is an aliphaticgroup with 1-4 carbon atoms or the group C₂H₄O(G)_(p); G is a saccharideresidue that is connected to the polyethyleneoxy chain by a glycosidicbond and p (the degree of polymerisation) is 0-10; Σp is 1-15; EO is anethyleneoxy group; s is 0-12; Σs is 2-15; Z is an anion and z is thecharge of the anion Z, except that p in the group R₁ is
 0. 12. Acationic sugar surfactant of general formula III

where R is an aliphatic group with 6-24 carbon atoms; R₁ is an aliphaticgroup with 1-4 carbon atoms or the group C₂H₄O(G)_(p); G is a saccharideresidue that is connected to the polyethyleneoxy chain by a glycosidicbond and p (the degree of polymerisation) is 0-10; Σp is 1-15; EO is anethyleneoxy group; s is 0-12; Σs is 2-15; Z is an anion and z is thecharge of the anion Z.
 13. A surfactant mixture which comprises acationic sugar surfactant of the formula:

where R is an aliphatic group with 6-24 carbon atoms; R₁ is an aliphaticgroup with 1-4 carbon atoms or the group C₂H₄O(G)_(p); G is a saccharideresidue that is connected to the polyethyleneoxy chain by a glycosidicbond and p (the degree of polymerisation) is 0-10; Σp is 1-15; EO is anethyleneoxy group; s is 0-12; Σs is 2-15; Z is an anion and z is thecharge of the anion Z; wherein the mixture also contains a quaternaryammonium compound of the formula:

where R is an aliphatic group with 6-24 carbon atoms; R₁ is an aliphaticgroup with 1-4 carbon atoms or the group C₂H₄O(G)_(p); G is a saccharideresidue that is connected to the polyethyleneoxy chain by a glycosidicbond and p (the degree of polymerisation) is 0-10; Σp is 1-15; EO is anethyleneoxy group; s is 0-12; Σs is 2-15; Z is an anion and z is thecharge of the anion Z, except that p in the group R₁ is 0, wherein theweight ratio between the cationic sugar surfactant and the quaternaryammonium compound from 1:3 to 9:1.
 14. A clear and stable, alkalineaqueous cleaning concentrate, which comprises 0.5-30% by weight ofalkali and/or one or several inorganic or organic alkaline complexingagents; 0.5-20% by weight of a surface active nonionic alkylene oxideadduct; and an amount of 0.2-20% of the mixture of claim
 4. 15. A clearand stable, alkaline aqueous cleaning concentrate, which comprises0.5-30% by weight of alkali and/or one or several inorganic or organicalkaline complexing agents; 0.5-20% by weight of a surface activenonionic alkylene oxide adduct; and an amount of 0.2-20% of the mixtureof claim 13.